MicroStrategy Eyes Revival of Bitcoin Tax-Loss Harvesting for Tax Benefits
MicroStrategy has long used corporate funds to accumulate Bitcoin. When prices fall, it can sell positions carrying unrealized losses to offset other capital gains and reduce its tax liability. The company first used the strategy on December 22, 2022, when it sold 704 Bitcoin for about $11.8 million in cash.
Executive Chairman Michael Saylor recently confirmed that the company, now called Strategy, is preparing to resume tax-loss harvesting, but it has not disclosed the amount of Bitcoin to be sold, the transaction value or the execution date. Following its 2022 sale, the company repurchased 810 Bitcoin for about $13.6 million on December 24, realizing a deductible loss while maintaining its overall exposure.
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The history behind this eventStrategy Recasts Bitcoin Treasury Model as Funding Pressures Rise
Strategy, formerly MicroStrategy, began as a business-intelligence software company before co-founder and Executive Chairman Michael Saylor redirected its balance sheet toward Bitcoin. It made an initial $250 million purchase in August 2020 and subsequently funded further acquisitions through common stock, convertible notes and preferred shares. The structure turned MSTR into a leveraged corporate vehicle for Bitcoin exposure, but unlike a spot ETF, investors also assume operating, financing, governance and capital-structure risks.
As of Aug. 28, 2026, Strategy held 840,447 Bitcoin acquired at an average price of $75,653, with the reserve valued at about $66.79 billion. Since May, the company has sold 6,948 Bitcoin for roughly $432.5 million to help fund preferred dividends and STRC repurchases, replacing Saylor’s long-standing “never sell” posture with a goal of never becoming a net seller. Strategy now weighs Bitcoin sales against equity issuance based on relative cost, while separate USD Reserve and unrestricted USD Cash pools provide liquidity for debt, dividends, buybacks and market opportunities.
Michael Saylor Proposes Selling Bitcoin to Fund Dividends as Strategy Posts $12.5 Billion First-Quarter Loss
Software company Strategy, the world’s largest publicly traded corporate holder of Bitcoin, has long been known for an uncompromising buy-and-never-sell strategy. Executive Chairman Michael Saylor’s proposal to sell Bitcoin to fund dividends breaks with that previous pledge and signals a more flexible approach to capital management. The move shows the company confronting the realities of capital markets and has prompted investors worldwide to reassess the viability of crypto-heavy balance sheets.
Strategy reported a first-quarter net loss of $12.54 billion and still holds 818,334 Bitcoin. To raise funds for dividends, the company sold 3,588 Bitcoin for the first time between June 29 and July 6, 2026, generating about $216 million. The move raised market concerns: JPMorgan warned that the policy would add “two-way risk” to crypto markets, while Fortune warned that Strategy could fall into a death spiral.
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